I wonder how many people have the cohones to truthfully respond to this question?

I will allow you to be anonymous and won’t spill the beans if I know who you are, I promise ;)

My confession:

A bedpost. Oh I know what you’re thinking. Like this, right? No no. no. The one in question was more like this. Yes it was long, and I yanked it off the bed. Yes I was desperate for anything that had a chance at helping me orgasm since I had nothing that could vibrate.

Why was it dumb?

1. Because it was probably dusted at some point using a chemical spray, like Pledge.

2. The accidental ramming of my cervix resulted in an hour or two of moderate cramping and spotting later on.

Back in my youth I used Suave Strawberry Essence shampoo to lube my penis. At the time I hadn’t learned to masturbate without any lubrication and, like you, was desperate to get off. Didn’t wash it all off thoroughly, though. Spent the next week with extremely painful dried, cracked skin on my penis. NOT. FUN.

Why was it stupid to use this as an anal sex toy? Because it had broken off the saucepan and there was sharp metal on one end and nothing to stop the entire thing getting sucked in had I loosened my grip. Luckily I’ve learned my lesson since then :P

The first time I ever tried anal play too!

~Sadly it’s how many start out, I think. Too shy/unsure to purchase an actual anal play sex toy.

When I was a young man I would use a vacuum cleaner. The hose end, and put my cock up in it. It ultimately worked but some times was painful because I would be hard and swell and was thicker that the inside diameter of the hose.

I’m sure I’ve done a bunch of stupid ones in my younger days (and maybe even slightly older days), but probably the stupidest three are below:

1) Screwdriver handle – it was a slightly bulbous one rather than the usual kind
2) Cork-stoppered glass bottle for some kind of bubble bath or something – a long, thin triangular pyramidal one which was an “I don’t know you” birthday/Xmas gift
3) The handle of a plastic Hallowe’en devil pitchfork… which I still have in my house

The most dumb of these being that I put potentially fragile glass up me and that the end of the pitchfork was basically a plastic tube with not-so smooth edges. Not safe, not clever.

Luckily at the time I hadn’t really worked out masturbation properly yet and was mostly experimenting with gently fucking myself with whatever seemed about the right shape. I was hugely curious and also massively ashamed during this period of my life (in a lovely binge/purge cycle like my early porn habits) and was super keen to figure out how sex and wanking worked.

It didn’t really work, but I guess I did learn a bit about my genitals, so yay. Ha, now wondering if I’ve been *too* honest! :P

~ I think most people have done this stuff, but just won’t admit it ;)

Margarine (which was just gross, not really dumb)… St. Ives Apricot Scrub (with the little grainy exfoliating bits), which hurt like a MoFo… and when I was a very young man exploring my sexuality and questioning my orientation, there was a VERY ill-conceived encounter with a plunger handle :-/

~If you were questioning your sexuality that’s one thing, but your wording leads me to believe that you questioned it because you enjoyed anal penetration? Which, enjoying prostate/anal penetration/vibration/etc has absolutely nothing to do with your orientation.

An egg. I once took a hard boiled egg and was having a great time, but I guess as I got more aroused my PC muscles sucked it deeper inside of me and it became temporarily ‘stuck’. I couldn’t push it out, couldn’t feel it when I reached in because it was too deep. I was in a panic and finally after a bit I did manage to push it out but I was terrified until then, thinking of how I would explain that to a doctor…

A good point, and perhaps my initial comment was poorly worded. I was already questioning my orientation due to other factors; that’s just the frame of mind that initially got me open enough to explore anal penetration to begin with.

It’s very true that the correlation between male anal penetration and orientation is purely stereotypical. I meant to imply that I experimented with anal because I was questioning my orientation, and it never dawned on me that I might like it until my orientation came into question. I did not question my orientation just because I was curious about receiving anal.

When I was 7 I discovered my mother’s Wahl-like vibrator and thought I’d invented that use for it. I stole it from her when I was 9 and realized years later she probably used it for the same thing. She stole it back from me when I turned 18.
I also used my dad’s pager and one of those squiggly vibrating

Vicks Vaporub. It was awesome for the first couple of minutes, but then, with a force that was devastating, it became first unpleasant, then painful, and then excruciating. Over approximately 15 seconds, it spanned that trajectory.

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